In 100 words: On the surface, Holiday glows with warmth and effervescence that few films can match. Its cast banters with witty abandon and its magnetic lead stars frolic with acrobatic grace. Its beats may be familiar but the script runs away from the safe and obvious. Yet beneath its joyful exterior, there’s a sad undercurrent nested in its pessimistic view of wealth that makes it different from genre mainstays. Not to mention Cukor directs the hell out of this: precise editing and smart mise en scène reveal characters’ shifting relation to their environment. Hepburn and Grant make a timeless and luminescent couple.

Other Movies for Context: Ah the Golden age of Romantic comedies, back when it was not a toxic genre, was full of interesting films that had something interesting to say about wealth amid the Great Depression. I’m thinking right now of Leo McCarey’s The Awful Truth (1937) and especially Gregory La Cava’s My Man Godfrey (1936). The Hepburn-Grant-Cukor-Barry team will make another film that summons the same magic they cast here: The Philadelphia Story (1941). Grant and Hepburn also teamed up for Howard Hawks’ real oddball Bringing Up Baby (1938) too. Among the modern films, look no further than the essential perfectness of Rob Reiner’s When Harry Met Sally (1989), a film I found difficult to leave off this Top 100 list.

In 100 Words: A complex portrayal of devotion, Almodovar’s masterpiece audaciously blurs the line between love and obsession, care and harm, all the while testing the limits of his audience’s sympathies and moral boundaries. Inspired by dance, older films, and music, his formal control here—emotionally charged colors, expressive design and cinematography, haunting score—adds dimensions to a script that perversely refuses to demonize its characters’ worst impulses and transgressions. But beyond its technical sublimity, this is the rare film to depict men who have feminine qualities without questioning their masculinity, while exploring the different ways people choose to communicate with each other.

Other Movies for Context: I adore Pedro Almodovar, and his filmography is divine, always smartly mixing melodrama with farce and comedy, while still being able precise about human sexuality, how they relate to one another, etc. I’ll start with Volver (2006), my personal favorite of his, along with All About My Mother (1999) and Women on the Verge of a Nervous Breakdown (1988). Tie Me Up! Tie Me Down! (1990) is pretty good too, even if it is a little icky, storywise.

In 100 words: In a national cinema that has confronted its turbulent past, none wrestle with history quite as achingly as Sopyonje, a moving allegory of a transitioning country. Part musical, part family drama, and part history lesson, the film’s powerful emotional expressions revolve around the rawness of pansori. At the same time, the film’s visual and sound designs suggest a director mourning a vanishing world: they capture the inherent tension between past and present that foregrounds Korea’s rapid modernization, as his itinerant performers are slowly becoming obsolete, along with the culture and values that once represented the soul of the Korean people.

Other Movies for Context: Im Kwon Taek has made so many films, some of which depict the tension between the past and present. Among the ones I’ve seen, several are fitting companions to Sopyonje: His film Chi-hwa-seon (2001) won him the Best Director award at Cannes, and portrays a painter who has gone insane. Chunhyang (2000) visualizes a traditional pansori song while using the artform’s recitation as narration. And Festival (1996) portrays Korean traditions as viewed from a modern lens.

dir. Jean-Luc Godard (1960) scr. Jean-Luc Godard based on a story by Francois Truffaut cin. Raoul Coutard with Jean-Paul Belmondo and Jean Seberg

In 100 words: Released in 1960 and forever changing the face of cinema, Breathless embodies the spirit of the French New Wave by essentially chucking the rigid rules of old movies out the window and playfully experimenting with form. The film was shot with a realistic vibe that approximated documentaries, invented new ways of shooting and cutting films, and created a sound that mixed colorful selections of jazz and Parisian street noise. But most importantly, Breathless effortlessly bridges the old and the new: it is a lovely homage to the films of yesteryear while it simultaneously points the direction for the medium’s future.

Other Films for Context: Godard is arguably the most famous and most important director of the French New Wave, making a lot of movies during the decade that influenced countless directors since. My favorite from the ones I’ve seen of his is Vivre sa vie (1962), a gorgeously shot and easy to follow movie. Other films of his I’ve seen include the overrated Contempt (1963) and the interesting Alphaville (1965). Towards the end of the decade, his works have started becoming more political and experimental to the point of being obnoxious–Weekend (1967) is a prime example of this turn.

In 100 words: Often cryptic and deeply unsettling, Terrorizers set the foundation for New Taiwanese Cinema’s exploration of ennui and disaffection in post-war Taiwan. Yang’s cynical vision of modern urban life in Taipei presents characters that are in one way or another, stuck in purgatory, who are then undone by a series of coincidences. By employing Bressonian edits, cinematography that captures a dreamlike plasticity, and Ozu-esque framing of space, Yang perfectly visualizes emotional violence and internal desperation succinctly without becoming completely abstract. The script’s amorphous structure yields uncomfortable surprises, but the startling conclusion may actually be that living is the most terrifying thing.

Other Movies for Context: Essayists have often compared Yang’s film to those of Michaelangelo Antonioni’s, particularly his London-set Blow-Up (1966), about a photographer who think he captured in pictures a murder in progress. But The Terrorizers is very important in Taiwanese film history for paving the way for Tsai Ming Liang and other Taiwanese directors who focus on Taiwanese urban life. Tsai’s Vive L’Amour (1994) and What Time Is It There? (2001) are the most direct films that reference Yang. A more distant, and uh cringe-inducing brother of this movie, will probably be Paul Haggis’s Crash (2005), but that’s cow poop compared to this.

In 100 words: The definitive portrayal of racism in America, Lee’s angry and raw film takes place on the hottest day of the year, and it shows. Characters simmer with resentment as tempers flare with the temperature, culminating in spectacularly shot, choreographed, and edited chaos. The film’s incredible mixtape of protest rap songs and sensuous R&B grooves sets the tone for the film’s rage and grief, while Lee’s muscular direction and singular style inject tension and urgency within its humor-filled script that miraculously never lapses into didactic polemics. Its relevance today proves the film’s prescience, as much as it shows America’s depressing state.

Other Movies for Context: Spike Lee has a distinctive filmography that’s worth checking out. My favorite other than this is Malcolm X (1992), his ambitious autobiography of the civil rights leader. The early 1990s also saw movies about contemporary African American issues released; most of them owe a lot to Lee’s influence. John Singleton’s Boyz n the Hood (1991) and Allen and Albert Hughes’ Menace II Society (1993) are both worth watching from the ones I’ve seen.

In 100 words: Oscillating between cerebral and esoteric, Assayas’s engrossing and frisky metatextual film about filmmaking has plenty of jokes about the cinema and the people who make it. Its characters argue passionately about what exactly is ruining the state of current cinema, whether it’s intellectualism, the money-grubbiness of American movies, or the lack of inventiveness from new directors. But if the film sounds like an excruciating exercise in self-criticism, fear not. It’s full of hilariously neurotic backstage personalities that are all trying to survive, while Maggie Cheung, in a black latex bodysuit, is just trying to stay above it all. Bracing end.

Other Movies for Context: Sad to say that this is my first and only experience with Assayas’s work. I see frequent comparisons to Francois Truffaut’s Day for Night (1973), which I also haven’t seen. When I listen to these people have very ,casual and intellectual conversations, I think instantly of Mia Hansen-Love’s Things to Come (2016),which may not be as frisky or as playful as Irma but still engages you to think just as much.